Look up a little Manga called Berserk. A character named Griffith is literally the greatest villain of all time.

He begins as an ally of the maincharacter. He is the leader of a mercenary band that conquers armies for the main kingdom within the story. The
mercenary band gains acclaim, fame, and knighthood. Trust, friendship, brothers in arms....everything all around. You're presented this for volume
upon volume upon volume. Griffith is a pretty cool guy and the maincharacter has grown softer in his relationships with others due to Griffith.
Everything seems fine until...

Well, you'll have to look up Berserk and read it yourself. I could do no justice explaining it. It is the greatest betrayal in literary history. I do
not use that last statement lightly. I can tell you that you'll be physically ill for a couple of seconds to minutes as you begin to process it all.
Good luck, because oh man...it just...dear God.

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